The Endlessly Fleeting Lives of Tom M Riddle
by Repenting Sirens
Summary: There once was a boy named Tom Riddle; he was a terrible person across all sorts of dimensions. Now he has to fix his transgressions across time and space, with the aid of 'Harry' (or rather Death himself). "The wickedness of the wicked shall be upon himself", indeed.
1. Near Death Experiences

**Author's Note** : Greetings fellow readers! This is the first time I've posted a Harry Potter story! I'm not gonna lie, this came from a really weird combination of thinking of winter and listening to sappy K-Pop songs ("I Swear" by mega cuties, SISTAR). I'll try to update regularly. ( ´▽｀)

 **Warnings** : There's gonna be a lot of exposition and description in this chapter as I plotted it out as a one shot and eventually realized that it was simply too impractical as it was. So it's pretty heavy in so far. It'll get lighter and easier to digest information-wise later on; sorry for the trouble.

* * *

 **H** e shut his eyes, letting the frigid darkness pool over him; it easily seeped through his threadbare blanket.

The night felt moonless and starless, like black ink had spilled across the sky and blotted out any light it had found in the ancient skies.

Nighttime in Wool's Orphanage always felt like that, as the world outside drifted in and he was simply left to drown in it.

He shared his room with no one, which was a surprising fact, considering the pitiful state of the orphanage. In the light of day he was able to use the room as a place of comfort and solitude, to escape the resentful, angry and jealous looks the other orphans would shoot him when they thought he was unaware (which was a hugely stupid move on their part; Tom would never let down his guard enough to be considered "unaware").

Yet the state of roommate-less-ness left him lonely (not that he would ever admit it to anyone). He had no friends in the orphanage and while the 'friends' he had made at Hogwarts were far better, he still needed far more companionship and interaction than an average snake could provide.

Tom scoffed at his own thoughts and banished them from his mind. He had never needed anyone to keep him company and he certainly wasn't going to change that now.

With a sigh he turned to his side and burrowed deeper into his blanket, eventually drifting off into a deep sleep, even as the world grew colder and colder around him.

* * *

It was snowing.

Everything was a flurry of white and cold, with the snowflakes that fell being the only source of light in the colorless world he found himself in.

The sky that hung above him was dark and empty, as if all of the stars and planets that had clustered the heavens had simply fallen away.

The snow on the ground was already tread on, with a single set of footprints leading into the dark depths of the overgrown forest. The trees themselves were a oddly majestic sight, with rust colored bark that was reminiscent of shiny scales, long twisting branches, and trunks that seemed to never end. They were completely alien against the wintery landscape, especially with the insolent leaves that clung to the branches themselves and the sheer volume of them. They seemed more like heads sprouting from serpentine necks than leaves.

He felt compelled to follow the path before him, knowing instinctively that it was intended solely for him and that no harm would befall him if he followed it. It was a feeling he rarely got, especially as a particularly skeptical and cynical boy.

Concealing his curiosity, not intentionally but rather out of force of habit, he followed the footprints which seemed to fit his feet and his usual stride perfectly. The wind around his form seemed to howl with excitement.

Walking forward, he was almost grateful to have the falling flakes to illuminate the way for him, as the forest around him seemed to only grow darker as he progressed. With that in mind, Tom tripped over an exposed tree root that had been shrouded in the darkness.

He grunted and shrugged the snow off of him, stopping to fix anything that might have gotten rumpled in the fall. It was another one of his learned habits that he gained from his time in Slytherin; you either kept a perfectly manicured appearance or fell even further down the social hierarchy.

The previously howling wind began to grow in intensity, until it became a deafening roar and he was forced to cover his ears. Then, he heard a clear voice amongst the noise:

"RIDDLE, HURRY UP!"

He stopped his preening and stood, noting that the once clear footprints had begun to distort and become more beastly in form. They still showed a somewhat clear path, despite having become more erratic and spotty, rather than the previously linear prints. The bright snowflakes also seemed to have dimmed, leaving the path even less visible than it had been when he had managed to stumble and fall.

He burst into a sprint, following the steps as far as he could until he came upon a fork in the path laid before him. The steps seemed to disappear completely, not even a hint of their forms left. He was at best confused, and at worst lost, as whatever had been leading him previously had decided to let him choose his path.

The rightmost path seemed to radiate a sort of overbearing heat, at odds with the wintery atmosphere. The leftmost path was forebodingly dark, with the same sort of frost that the world around it had.

If Tom were a boy to simply do the expected, to make the most natural of human choices, he would gone right; but Tom was not simply a human boy, he had been destined for more since his very conception. With his choice made, the strangely alluring voice that had called him before seemed to breathe a sigh of relief and the wind seemed to whisper "thank you" against his ears.

With that, he chose the leftmost path and followed it until his body felt like one with the cold and darkness that had endlessly surrounded him for what felt like years. He walked even beyond the darkness and cold and came upon what seemed to be the end of the once seemingly endless road.

Light poured in from between a curtain of overhanging leaves, which came from two smooth cream colored trees that poked out like sore thumbs amongst the sea of scaly trees, as well as a light minty scent; with a casual poise, he parted them and came upon what seemed like an impossible space in between the forest. It was a clearing, with light pouring upon a gigantic tree, with a steps carved into the sides and a large throne-like alcove, where a boy was seated.

He gave off the sense sense of being incredibly fragile, from his crisscrossed legs, to the thick black furred sweater that seemed to engulf his small frame. There was something off about him, that stretched beyond his strange appearance (from his fiercely sharp cheekbones to the thick white spotted eyelashes that were attached to his purple-veined eyelids and the odd black markings that seemed to be carved into the side of the boy's neck). It dawned on him as his eyes wondered off the black haired boy; the world around the haloed tree was midnight blue, as if the boy had stolen all of the light for himself. Even the sky itself seemed empty, besides the small hazy moon that seemed to shine solely on him.

"It seems that you made the right decision, even without my help!"

His mouth stretched into a cheeky grin, and any sense of wrongness that Tom felt easied off. Instead, he felt a burning curiosity to know what had lead to him coming here, to the absolute darkness that surrounded them, and all of the other oddities that had plagued him since he arrived.

The boy moved out of the alcove, and made so as to approach him, leading Tom to steel his gaze and step forward as well. There seemed to be no threat in so far but he refused to seem like a perfect victim if a battle were to come about. They stood face to face, with an odd resemblance between one another.

The boy put out his hand, and Tom hesitated before taking it and shaking it confidently, until he realized that the very same snowflakes that had once been leading him here were now sticking to his skin and seemingly merging into him, pushing painfully into his magical core.

He struggled to pull his hand free, as he screamed, anger and pain overwhelming his body. The other boy held onto his hand tighter, his face looking far grimmer than before.

The barrage of energy soon ended, and he went lax, and fell to his knees on the snowy ground, feeling like he'd been run over by a train. The boy sat down next to him, his seafloor colored eyes fixed on Tom's dark ones, and his face seemed to scrunch up.

"My apologies, Riddle, but I had to ensure that your connection to the prophecy was broken."

"Oh shove it," he bit out, clutching his aching abdomen. His body was still in pain from the forced energy transfer, and he was in no mood to hear some idiot give him a half-assed apology.

The boy shut up and waited for Tom to call on him; it was a oddly submissive gesture, doubly so on such a lithe boy.

Fearing that he'd never get any answers if he continued to let the idiot waste his time, as he dusted himself off. The snow was they were seated on was surprisingly warm.

"What exactly did you do to me?" His eyebrow rose, and his eyes narrowed as he impatiently waited for the other to respond.

The other seemed to be mulling it over in his head, almost uncertain of what to say in the face of a pissed off Tom Riddle. Honestly, what did he expect when he was pulling something like that.

He sighed and stared up at Tom through his strange eyelashes, as Tom was taller than Potter even while sitting. He seemed tired even to the naked eye.

"This is gonna sound very very strange, and possibly even a little dumb," Tom snorted, already certain that this speech was going to end terribly. The boy perked up a bit, and puffed out his chest. It seemed like things were going to get interesting, then.

"I am formally known as Death," the boy's lips quirked and his eyes seemed to glow, and Tom felt inclined to believe his words. He tacked on a "I was originally known as Harry Potter and I much prefer that though" with a quick grin.

Tom felt a need to roll his eyes but ignored it, urging Potter to continue talking with a quick hand gesture.

"This is your mindscape, which is the only place that I can truly access your magic without being rebuffed or having Fate interfere directly," Potter went on to explain and Tom's face looked like a sour lemon. He had recently begun to study the mind arts, and hadn't been able to gain access to the magical manifestation of his mind, while this person-thing-whatever had managed to casually slip in and make himself at home.

"I'm a literal god. It's not surprising that things come far more naturally to me." Potter said unhelpfully, shrugging his shoulders. Tom scowled at him in turn, wondering if he had somehow spoken aloud.

"No, but we're in your mind and I can quite clearly hear your thoughts; it's plain old rude to call someone an idiot, by the way."

Idiot. Idiot. Idiot. Idiot.

"Stop doing that and talk to me already, you tosser."

No.

"This is getting frustrating and childish. Can we just get back to the topic at hand?"

Fine.

"Verbal responses, Riddle."

"Fine." He grit his teeth.

"Oh good, you're finally feeling cooperative! Now, back to my main point: I came here to destroy the bond that tethered you to a prophecy that would eventually be made about you in this timeline if I didn't interfere. Now, you made the whole process actually possible by choosing to allow me to meddle with your mind and connect it to a realm where I am corporeal and can use my powers as I want along with denying Fate when they called to you, so thanks for that," Potter rubbed the back of his neck, a look of relief on his face.

"I thought it was going to be much harder than this to be honest; but then again, your magic was pretty permissive and seemed to recognize mine. Probably a byproduct of all of those timelines where we shared a soul..." He rambled on, and Tom perked up, wondering exactly how he'd ended up sharing a soul with a god.

"Do you want me to answer that question or should I pretend I didn't hear it?"

"Later. I'd rather you continue with what you were saying before you started to ramble."

Harry rubbed his chin, trying to remember where he left off.

"Oh! Right, well, that prophecy usually leads to terrible results, like the world being destroyed by overzealous maniacs or the muggles finding out about magic and bombing everything into submission and cleaning the earth in their own special way."

"What is that prophecy anyway?" Tom weaseled in, his curiosity rearing its head again.

"Well, I'm not actually sure anymore. It's been a long time since I've heard it and I usually don't make it this far with your other incarnations."

"Are you even useful for anything at all?!"

"I freed you from massacring your soul and the entire Earth. As a byproduct, I've had to repeatedly live through these encounters far too many times now and you should be far more grateful to have my assistance."

"So what you're basically saying is that you've had to replay these events over and over again across different timelines because you're incredibly incompetent?"

"When you put it that way it sounds so ugly, Riddle. Just appreciate my efforts here."

"I refuse."

"Well at least your stubbornness never changes. That's something I can always count on."

"Frankly, I've grown tired of your voice. Can I please just go back to my blissful cold slumber?" A yawn forced its way out of Tom's mouth and his eyes began to droop.

"Riddle, if you go now I ultimately will have to follow you back to your realm and guide you properly through this timeline."

"Yes, yes, fine, fine. I don't care, I just-just wanna go to sleep." Tom slumped onto the ground, his skin rapidly paling.

Potter looked around at those words and a panicked expression showed up on his face.

"SHIT. I kept you here too long; the realm is absorbing your mind. I'm going to send you back now. Just hold on a little longer."

Tom felt chilly hands touch his back and he was suddenly face down in the snow, as the hands seemed to be trying to push him through the ground itself.

It was horrible and awful and terri-

* * *

He woke up, in his bed, the darkness and cold that had previously surrounded him dissipating. With a start he realized that he felt like a train had run him over, once again, and he felt more tired than when he had first gone to bed.

Took a quick peek to the nearby and it seemed to still just be settling into dusk, and he breathed a sigh of relief.

He was going to have a lot of things to deal with tomorrow and he certainly didn't intend to do so with barely a wink of sleep in his system.

With a yawn, he curled under his blanket and fell into a deep, dreamless sleep.

As his body stilled in its slumber, a pair of bright green eyes stared at him from the darkness.

"Sleep well, Riddle," he said, quickly checking the other's vital signs and then disappearing back into the shadows.

* * *

So, what did you guys think? I wasn't super satisfied with this chapter to be honest, but if I didn't release it into the wild world of Fanfiction soon, I probably never would. It'll also be more humorous as we go on; I got too caught up in serious info vibe to be funny. **OTL**


	2. Dead and Dying

Previously known as "Rinse, Repeat" with a different summary.

I got really anxious about writing this story in general and basically turned into a pile of useless putty. Sorry for the long wait, enjoy.

Parseltongue usage is denoted by these little guys: «_ _ _ _» with actual words of course.

Warnings: None for this chapter in particular.

* * *

He hissed under his breath, anger leaking out of him like drumming rain. The orphans he reluctantly shared his oxygen with were daft little things, and far too loud for the time of day it was. He poked at his porridge and scoffed, noting that once again their rations had been cut and the matron had been forced to creatively ladle the food so it would appear more plentiful.

The overhead lights that illuminated the mediocre-looking room were placed haphazardly, reflecting unevenly off some of the more beaten up tables and chairs. It was a miracle that they even had furniture at all, considering how useless their caretaker was with the orphanage's budget. She was almost painfully negligent as well, a fact that everyone who had been in Wool's long enough knew.

"If they bother you that much I could just dispose of them all," A cheerful voice said from his left hand side, startling him into biting his cheek. He bit down the yelp that naturally wanted to escape his lips and turned towards them.

The being, or Harry as it prefered to be called, waved at him casually, an easy smile on his face.

Tom hissed under his breath, memories of the horrible dream from the previous night rushing to the forefront of his mind; although, it couldn't simply be a dream now, seeing as the one who previously interrupted his beauty rest was here. He pushed his less than pleasing breakfast away, a deep scowl on his young face.

What a pity that it hadn't been a dream after all.

"What do you mean by 'dispose of them'?" His eyes narrowed, unpleasant feelings welling up inside of him. He wasn't a practiced killer yet but the idea that he would need someone else to do his dirty work for him was easily an offense against his person.

Harry quirked his head to the side, a look of amusement crossing over his face. "I'm the personification of Death, Riddle, what do you think 'disposing' of someone means to me?"

Riddle's cheeks flushed, which only served to further invigorate his previously in check spite against the other, and he almost replied when he heard one of the more obnoxious kids whisper "why is Harry talking to Riddle?". It served as more proof that Harry was indeed real and not just a figment of his imagination, but the implied familiarity didn't sit well with him at all. How could any of them know the being's name when it was the first time he had ever shown his face in the orphanage?

Having realized the danger of openly talking to Harry in front of the lowly muggles before him, he dragged him off to his pitifully sized room. It was certainly more private than the mess hall and wasn't contaminated by muggle filth, which was always a plus. It also allowed him to relax somewhat more, less afraid of having a personality slip in front of one of the orphanage workers.

With a regal ease he sat down on his bed, leaning back against the wall as he lazily drew his right leg up as the other hung over the edge. Harry stood near the closed door, as if waiting for an invitation to sit; well Tom certainly wasn't one to be rude to guests, no matter how unwanted they were. He motioned to the chair nearby and waited.

"Why are you here? Why do they seem to know you?"

"Don't you remember that I said I'd have to come back during our last meeting? I expected you to have a far better memory than that, Riddle," Harry teased, a cheeky look on his pallid face.

Tom's earlier scowl returned, although more malicious this time around. One might even believe that he might descend from a line of basilisks due to the intensity and hatred in his eyes. If Harry wasn't death itself and a reckless Gryffindor to the base of his soul, he might have felt fear, but he was what he was and the look he got was rendered ineffective.

"I'm a magical prodigy, top of my year in both skill and knowledge. I would never forget such information, no matter how insignificant," a haughty look graced his features, "asides from that, you seem to have tried to evade my second question. Answer it."

Harry threw his head back in a clear, chilly laugh, as if he hadn't managed to find something quite so funny in so long. The coldness in his laugh seemed almost at odds with the attitude and mirth that the be-boy (frankly, if the be-boy wanted to have a play at being human, Tom would humor him; it was only the polite thing to do, of course.) had presented to him since their first meeting. The coldness wasn't unpleasant per say, just strange. Then again, nothing about death would ever seem normal to him. He felt a small shiver at the thought.

Harry calmed down once more and cleared his throat. From what Tom could see, the boy didn't exactly need to breathe to speak, so the throat clearing must have been a habit from his prior days.

"It's one of my job 'perks', you could say. Death is a normal part of existence, meaning that I'm technically known to all those who exist under my jurisdiction." Harry scratched at the back of his neck, another potentially leftover tick from his past life.

How strange, indeed, he thought and rolled the information he had gleaned over in his head. The phrasing for the last sentence had been strange, almost a hint at something else.

"All of those who exist under your jurisdiction?

"Those who can succumb to death. Most things on this planet fall under that category but some," Harry shot him a deeply unsettling look at that,"have managed to escape my grasp. It's rather disappointing when they do. It's almost like they'd rather not meet me, for some reason."

"You say that as if you don't know exactly why no one wants to die and come across you."

As Tom spoke, he blinked and sat up properly at the new information, feeling his magic flare up joyously. A way to escape death, the ever looming shadow in his life? It was the most vital piece of information he had learned in a long time! Not only that, but he had heard such information from the mouth of the very horse he was trying to run away from. It was almost poetically sweet. Which of course, meant that it would be taken away from him. Nothing good ever lasted for him, it seemed.

"Oh no, no, no, Riddle. You will not be meddling with immortality this lifetime around. I've put in far too much work to have anything I've done fall apart due to your childish fears. Immortality is what lead to that accursed prophecy in the first and I doubt that I could destroy a second one of Fate's plans without having her full wrath come down on the both of us. No, you'll just have to settle."

"Settle? You think that we simply settle for death, like a consolation prize? Ha! Death is the most disgusting, putrid, thing that one could ever be forced to go through. It's an endless curse. The most easily exploitable weakness in life's design." He grit his teeth, fists clenching at his side. The boy-creature-being-thing seemed to only manage to agitate him, and bring out the worst in him.

The other looked at him with pity in his eyes at his words, and he saw red. The command flew out of his mouth in hisses, parseltongue coming more naturally to him than his native English in his rage.

«GET OUT»

«Riddle, do try and calm down.»

«LEAVE. GET OUT.»

Harry shook his head sadly, far more morosely than he had the right to be, Tom would have said if his mind wasn't clouded by anger. The other melted into the shadows, his once solid and boyish form becoming nothing more than darkness in mere seconds.

* * *

A week slowly passed by before Harry appeared once more.

In that downtime he had gotten a assortment of letters from his 'friends' sent via owls that were far too gaudy and conspicuous for his muggle surroundings. It was a wonder that the ministry had made it this long without their kind being discovered by crazed muggles. If given the proper power and funding, he himself would have instead set up a magic equivalent to the post office that would be far more direct and easy to use. Letters would be placed within a sealed bag, that would be keyed to a specific wizard or group that could only take the mail themselves. It was a great idea if he did say so himself. Tapping his fingers against his chin, he considered the logistics of the idea and decided to research it later.

As he flicked through the letters, he noticed that the shadows in the corner of his room seemed to pool together and darken somewhat.

"Your presence is incredibly conspicuous today." His acting skills had never come more in handy, helping him hide how wary he truly was under the relaxed appearance.

Harry shrugged, materializing fully, and took the seat by the bed. Tom's lips curled, and his eyes narrowed. Their last meeting had been less than pleasant, which seemed to be turning into a habit with their interactions, and he still hadn't gained all of the information that Harry had promised him a while back.

With a subtle gracefulness that he shouldn't entirely possess at the age where limbs were still growing and maturing, he drew closer to the other and used his right hand to rest his head against. He gave Harry a hazy look, his mouth twisted to the right like a snake that had managed to sink its fangs into a particularly tricky gazelle.

"You seem to keep forgetting your promise back in my mindscape. Are you really that inept?" Harry's eyes widened at that and a sort of anxiousness flickered across his face. It was a odd look for him, and Tom felt rather pleased when it disappeared from his face.

"I did previously mention the prophecy, yes?" Harry's eyes locked onto his face and he gave a nod.

"The prophecy usually lead to us sharing a soul; well rather, I would end up playing host to a piece of your soul while you went mad from a lack of it, but that's not the important part. Our situation is the typical way used to find new beings to play the roles of 'Life' and 'Death', since the roles are essentially two halves of the same coin."

Tom scoffed, ready to start up his previous "death-is-the-worst-how-dare-you" rant but Harry cut him off rather quickly.

"Yes, yes, I know you hate death and find it disgusting. It's not particularly necessary to repeat yourself, it certainly won't make me agree. As I said before, life and death are two halves of the same whole and need each other to work properly—"

Tom cut him off with a haughty look. It served Harry right for having cut him off before. "If you supposedly need a 'Life' counterpart, then where's yours? I'm not currently doing the job, so someone or something else must be doing it."

"Fate is currently taking over that role."

"Isn't Fate the meddling being that made that prophecy that constantly results in me destroying the world? Wasn't Fate trying to keep me from interacting with you in the first place?"

"It must seem rather odd to you, but it's generally how things are done. Fate is rather...meddlesome and creates tests to ensure that the one who becomes the Life god can handle it appropriately. In a similar vein, the prophecy is a sort of link way for the first versions of our soul. When the first incarnation of you put stock in the prophecy and helped fulfill it, he essentially validated that we were meant to be the new replacements. So it's all like a rather elaborate job application." Harry grinned broadly at him, as if he had said the funniest thing in the world. It rather conflicted with his eerie appearance.

"You said 'tests'; that implies that there are more than one. The mindscape interference doesn't seem like it would fully count as one, so what are they?"

Harry's grin seemed to somehow grow wider at that.

"You caught on quite fast. Well as the possible future god of Life, it seems rather contradictory that you've caused so many deaths; which is why you're going to have to repent for all of the deaths you've caused. Rather brilliant, wouldn't you say?"

"I haven't caused any deaths at all!" His face with taut, his hands slowly coiling into fists.

"Have you heard of original sin? It's a muggle concept, to do with the idea of the first transgression committed against their God being carried down by the descendants of that sinner. It's rather much like that. You," Harry's eyes seemed to lock onto his, an unreadable emotion in them,"have killed countless people across thousands of realities. It might not have happened in this reality, but you're going to be held responsible for it."

"That's not fair at all."

"It's not," Harry conceded, a smile slowly crossing back onto his face, "but life isn't fair either, is it?"

* * *

First chapter was posted on: July 9, 2015

This chapter was originally posted on: August 20, 2015


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